


A History

by DantheJerk, JMLeeds, KWMC



Series: TLKOE HEADCANON [1]
Category: The Last Kids on Earth (Cartoon)
Genre: Gen, Other, Other Additional Tags to Be Added
Language: English
Status: In-Progress
Published: 2020-06-13
Updated: 2020-11-04
Packaged: 2021-03-04 04:42:00
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence, Major Character Death, No Archive Warnings Apply
Chapters: 2
Words: 6,476
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24707776
Author URL: https://archiveofourown.org/users/DantheJerk/pseuds/DantheJerk, https://archiveofourown.org/users/JMLeeds/pseuds/JMLeeds, https://archiveofourown.org/users/KWMC/pseuds/KWMC
Summary: Fictional Bio and Info for canon and non canon characters of this fandom.
Series: TLKOE HEADCANON [1]
Series URL: https://archiveofourown.org/series/1786309
Kudos: 47





	1. Jack Sullivan

**Birth Name:** Jackson “Jack” Teague Duncan Macaulay O’Sullivan 

**Legal Name:** Jackson MacDonald Sullivan

 **Citizenship:** Dual American and Irish citizenry.

 **Irish:** _Síacás Tádhg Donnchádh Mácamhlaigh Ó Súilleabháin/Síacás MácDómhnáill Súilleabháin_

 **Likes:** Music (especially ones compared to that of Gorillaz, Daft Punk, and many others; with his upbeat personality being most influenced by reggae), his friends, June Del Toro, love from others as a family, video games, movies, comics, varieties of fiction in books and literature. 

**Dislikes:** "Sully" (short for his surname Sullivan) or Blackjack (because of his hair color and nickname being "Jack"), any other variations of his name (e.g. pallet-jack, the jack, flapjack, jack-hammer, jack-rabbit, etc.), any Irish racial names (e.g. Paddy), lonesome, corrupt father figures (is not so fond of male role models), his grandfather, being a pawn for others to use, bullying, racism, deception.

 **Family:**

  * Kieran Macaulay O’Sullivan (Father) †
  * Evelyn Saralee O’Sullivan (née Armstrong; Mother) †
  * 5 siblings (3 stillborn brothers, and 2 SID sisters) †
  * James Ryan Thomas O’Sullivan (Paternal Uncle) †
  * Tristan Owen O’Sullivan (Cousin; Son via Uncle James and Aunt Margaret) †
  * Margaret Diane (née Krueger; Margarette Diana Heidkrüger; Paternal Aunt) †
  * Charles “Chuck” Jonathan Kelly O’Sullivan (Paternal Grandfather) †?
  * Mae Ruth Jensen (née Belle; Paternal Grandmother) †? **  
**



**BIOGRAPHY**

Jack Sullivan was born as Jackson Teague Duncan Macaulay O’Sullivan in the Middlesex county town of [Belmont](https://en.wikipedia.org/wiki/Belmont,_Massachusetts), [Massachusetts](https://en.wikipedia.org/wiki/Massachusetts), on October 21, 1999 as the rainbow baby of Evelyn (née Armstrong, b. 1969 d. 1999) and Kieran O’Sullivan (b. 1968 d. 1999), honorably discharged veterans of the [Gulf War](https://en.wikipedia.org/wiki/Gulf_War).

Both his parents and uncle fell victim to a traffic collision while en route to the hospital which ended up taking their own lives; while his mother later died on her childbed from shock; leading the orphaned newborn into the custody of his paternally-estranged Irish grandfather Charles O’Sullivan (b. 1935). 

His grandfather, a Vietnam-veteran, was a spiteful drunk of a man with bipolar disorder, who at the time of his parents’ and uncle’s death, had also taken in Jackson's cousin Tristan (who 10 years his senior, was James’ only son).

As a career fisherman, Charles owned a large fishing yacht at [Provincetown](https://en.wikipedia.org/wiki/Provincetown,_Massachusetts) for himself and his friends back then, and wherein during the summers, used says vessel to catch seasonal grub for the food markets and also take shelter onboard if he was forced out of the latest domain that he resided in on land. His other jobs included him (and occasionally, under coercion, his grandsons) as a part-time salesman at the local flea-markets, apartment maintenance and longshoreman, with fishing being the only thing he’s good at.

**Early Years**

**(2 months old)**

Taken by his grandfather to be raised in his ancestral hometown of [Tralee](https://en.wikipedia.org/wiki/Dingle) before removing to [Killarney](https://en.wikipedia.org/wiki/Killarney) in the [County Kerry](https://en.wikipedia.org/wiki/County_Kerry) of [Ireland](https://en.wikipedia.org/wiki/Ireland) to be admitted to a [Naíonra](https://en.wikipedia.org/wiki/Na%C3%ADonra) (Irish-language Immersion nursery-preschool) for several years before eventually returning to the United States to live in his grandfather’s mobile home of Seaside Rd in the Irish-popular town of [Scituate](https://en.wikipedia.org/wiki/Scituate,_Massachusetts).

**School Years**

**(age 7-9)**

Due to his special needs, Jackson spent the majority of his youth being educated at the American Montessori school of [Inly](https://en.wikipedia.org/wiki/Inly_School) at Scituate. Though shy at first, Jackson eventually found a friend in both his motherly English teacher Nancy Foster and 5th Grade student (to whom he had a crush on), Kimberly Holland.

from there, learnt to speak English as he spoke [Irish](https://en.wikipedia.org/wiki/Irish_language) at home.

Because of the school's educational nature, Jackson was most into art, history and literature where his interest in music also began. Many of Jack’s teachers and peers included would grow fascinated as the boy's precocious knack and penchant for music and storytelling developed, becoming more heavily influenced by his cousin who he spent most of his time with while living under the roof of his nefarious grandfather; sharing his favorite records and albums ranging in genres from the oldies to the modern as he also had a talent for it. Through his cousin, who Jackson looked up to strongly like an older brother figure; Jack acquired a number of skills that will aid him in surviving the hardships that would later go on throughout his life including: basics in self-defense (tripping people, jumping high, running in leaps, bits and pieces of martial arts), having a tough facade to hide fear, and many other useful ones to add. 

This was also due to the fact of him being the target of much bullying in his neighborhood by older children. One boy in particular whose a skinhead preteen that lived in his neighborhood was named Buford Ferguson. Jackson, hearing the name Buford for the first time, mispronounced it due to his limited English and thus gave him the name “Buffer” for his ”obnoxiously tall and stout physique that weighed poor semblance to the Hulk”. Buffer victimized young Jackson with physical intimidation and verbal insults for his skinniness, quiet demeanor in social conventions and most of all, the times he was forced by his grandfather to perform in public. 

However, the bullying didn’t stop there either. At home, his mean-spirited grandfather was verbally and emotionally abusive towards him and Tristan while also being the most notorious in the neighborhood for his many addictions and sour attitude alongside being most infamous for (at least in his grandsons’ opinion) exploitation: A fact very clear as he had often forced the young Sullivan and his cousin to busking with their school instruments in public places (including bars, restaurants, and even near the forefront of grocery stores) for personal gain, especially monetary ones, with failures often ending in physical violence or meal deprivations. 

These are the result of Jackson’s shyness in expressing affectionate feelings and poor social skills to deal with any type of emotional reciprocation; giving reason to why Jackson isn't able to trust many people in such areas. Alongside this, his grandfather's behavior has caused several incidents to take place, including ones ending with them being banned from several public areas (i.e. stores, restaurants, and even entertainment centers) due to his bipolar disorder. Some of these incidents have caused Jackson to suffer from anxiety (or PTSD) when one time, his grandfather invited some new neighbors over into his home for a drinking session, which ended with him being heavily inebriated enough for them to take advantage of his grandchildren while they robbed him blind, traumatizing young Jackson into becoming selectively mute in the process.

After hearing about it from Tristan, Charles decided to get his act together and start by going to the local church down the street. When he did however, he became more stricter and overbearing on Tristan and Jackson, ending with them running away when he beat them for stealing some of his belongings to earn money for food.

In the summer of 2008, when he was about 8 (months away to being 9) years old, the drama of his life began. When Charles' behavior in the past decades ended up affecting the economy of the park, the mobile homes was thence bought by an airline company bent on converting it into a newfound flight lot. Charles, already angry from all the evictions, decided to live on the yacht he had at Cape Cod, disregarding his grandsons who wanted to stay as they had fond memories of the neighborhood. An argument between his cousin and grandfather ensued, ending with Tristan taking Jack onto his motorbike and leaving Charles behind. But Charles, stubborn and infuriated, chased them down in his SUV, causing a serious car wreck to badly injure Tristan and put Jack into a year-long coma after suffering [traumatic brain injury](https://en.wikipedia.org/wiki/Traumatic_brain_injury) which became post-traumatic amnesia (when his helmet flew off due to him being small). Charles was arrested as a result of this injury, and the family having already struggled financially, ended up having his youngest grandson put into foster care while Tristan remained at the hospital for a couple months.

It would be the very last time Jack got to see his cousin again with the memories he lost being the ones involving his cousin, friends, and the good times he had, with the bad ones remaining to embitter him.

Before he ended up fully enabled into the fostering system, the officials in the Social Work Program legally changed Jackson's name to its current status [Jackson MacDonald Sullivan] as means to divert his grandfather from tracing him; and nicknaming him "Jack" upon awakening in the hospital.

**Foster Care**

For three years, Jack would go around the state counties of [Middlesex](https://en.wikipedia.org/wiki/Middlesex_County,_Massachusetts), [Norfolk](https://en.wikipedia.org/wiki/Norfolk,_Massachusetts), [Plymouth](https://en.wikipedia.org/wiki/Plymouth,_Massachusetts), and [Suffolk](https://en.wikipedia.org/wiki/Suffolk_County,_Massachusetts) while in the foster care system, many of the households he experienced had similar effects on him like when he lived with his grandfather; with each of the past families whose house he'd been in brought back vague but sporadic memories of the same events with Charles, serving to make him the more bitter and distrustful as he was reminded of his past. 

It wasn't until the latest home he arrived in would be that of the Robinsons' household in [the year 2012](https://en.m.wikipedia.org/wiki/2012_phenomenon) at age 13, where he knew (like before) that he be used for their own reasons (e.g. doing most of the chores at home). 

**Pre-Apocalyptic**

Arriving at [Wakefield](https://en.wikipedia.org/wiki/Wakefield,_Massachusetts)’s Parker Middle School while living with the Robinsons, it initially seemed things wouldn’t meet change for young Sullivan who was painfully shy and distant with others, being apprehensive in close connections. And once again as before with Ferguson, Sullivan faced unjust persecution, mostly from an over-age student held back in the 8th-grade named Dirk Savage who procured from him most of his lunch money. It wasn't until his bad grades in math and science got him to be partnered up with fellow classmate Quinton “Quint” Baker; who helped Sullivan improve his grades by being his personal tutor and eventually first and only friend in so long while he also developed an infatuation with a girl star student named June Del Toro; whom he met after the second semester in Photography class. His friendship with Baker strengthened when the world collapsed under the unexpected period of the Monster Apocalypse. 

**Ancestry**

Jack’s adoptive paternal seven-times-great-grandfather Teague Moriarty O’Sullivan was the eponymous progenitor of the Sullivan name; as the akin patriarch Duncan Macaulay of his six times-great-grandfather was actually from the Scottish Herbides on an evangelical mission from Ulster died from disease during the [Famine](https://en.wikipedia.org/wiki/Great_Irish_Famine), leaving his pregnant Irish Presbyterian widow to remarry his best friend O'Sullivan who became the stepfather of their child. Leaving his hometown of [Dingle](https://en.wikipedia.org/wiki/Dingle) in the [County Kerry](https://en.wikipedia.org/wiki/County_Kerry) of Ireland in 1850, the O’Sullivans arrived at Provincetown, Massachusetts, staying there a couple months before moving through Scituate and settling in permanently at Boston. 

Duncan Macaulay O'Sullivan (c. 1846-1926), Teague’s adopted firstborn, in his early twenties, joined the Union Cavalry Recruitment in Worcester by the time the Civil War erupted, fighting in the Battles of Antietam and Gettysburg. After the war, he married and had three children.

His mother, Evelyn Saralee O’Sullivan (née Armstrong), was mostly of Scottish ancestry, with some German, Welsh, French, English, and Jewish descent.

Jack's maternal grandfather Lawrence (b. Raleigh, NC, 1945–1967) is of Scottish and English heritage dating back to the American Revolution; whilst his maternal grandmother’s side is descent of Welsh and Scottish ancestry from her mother Mary Allen (née Davyn) Armstrong who is also descent of German and French ancestry with Jewish from her mother Ida Saralee, who was a British-liberated prisoner of Dachau during World War II.

 **Bilingualism**

Jackson’s native tongue is [Irish (Gaeilge)](https://en.wikipedia.org/wiki/Irish_language) which he spoke at home since toddlerhood until he attended Inly, making English his second primary language intermediately then. Taught by both his grandfather and cousin alongside some of the Inly school teachers who also spoke it; Jack completed his Irish by the time he turned thirteen, in spite of the fact he seemingly adheres no noticeable accent, he does have a small lilt in the back of his voice.

**Religion**

As a member of a sixth-generational Irish-American family on his father's side, Jackson was brought up in a strict [Irish Catholic](https://en.m.wikipedia.org/wiki/Irish_Catholic) household under his grandfather Charles (who was a [lapsed Catholic](https://en.m.wikipedia.org/wiki/Lapsed_Catholic)) for the majority of his youth. During the interim of these rough times (before becoming a foster child), he was tutored and loved by his motherly Inly school teacher Nancy “Nan” Foster; who unbeknownst to him, was his best friend’s (Quint’s) maternal aunt. Through Foster who was full of positivity and faith; Foster took him to her local Baptist church on Sunday’s when his grandfather was out drinking or unconscious. From Nan, he also called God “Papa” like an old friend. **  
**

However, the lasting calamity with his grandfather (and later, the continual abuse from every foster household he’s arrived in) waned his beliefs. Despite losing his faith as he felt abandoned, Jack kept his cousin's leather bible as the only memento to maintain hope.

After discovering his mother’s Jewish heritage, Sullivan began learning Judaism, but relented upon learning that they didn’t share the same messianic views of Christ and thus became a deist bordering on Agonistic Atheism. But eventually becomes a born-again (and non-denominational) Christian after saving his friends during the Monster Apocalypse, counting his blessings daily. His faith is not always up to date as he isn't too uptight, due to some doubts inhabiting his fears but still prays every night.

 **TRIVIA**

_**A/N:**_ Leeds and I chose the name Jackson as we felt it be appropriate for Jack to have an ACTUAL full name. The foreign spelling of it beneath is the Irish (Gaeilge) version of his name; reason for this being that de facto, there is LOTS of Irish living in Massachusetts since the Civil War, more than New York and California combined. So we chose the towns carefully. 

The reason we chose such a rather LONG NAME is because in our minds we thought it be perfect to fit the meaning of his name(s) into characteristics which makes him... well him. 

We didn't do the ancestry or birthday thing out of creativity (a little bit of that goes to Leeds and our Friend Kyle), most of this is based off facts and knowledge we obtained by thorough research. For example, Jack's heritage is partly based off his actor Wolfhard whose (date of birth we took from) was actually Irish, Scottish and Welsh descent from his parents while the rest of his heritage is mostly German, French and Jewish alongside many others that we cannot say. His place of birth was also based off his creator himself, Max Brallier. 

Because Jack is often the one telling us the story in almost every TLKOE book, so we gave him the name Teague (i.e. Poet, Storyteller) thinking you guys can concur with this. And since Kyle pointed out that his surname is Irish in origin, and because he has BLACK HAIR BTW (fitting (one of) the typical Irish looks "[Black Irish](https://www.google.com/search?q=Black+Irish&rlz=1C1GCEU_enUS851US851&oq=Black+Irish&aqs=chrome..69i57&sourceid=chrome&ie=UTF-8)"), we gave him the name Duncan which can mean dark or dark-haired warrior, justifiable in my opinion at least. Leeds was the one who had since loved Home Alone growing up, learnt that the name of the actor playing Kevin McCallister, Macaulay (which means "Son of righteousness") we had to agree upon that name. And thence, Jack Sullivan, or better yet known by his birth name, JACKSON Teague Duncan Macaulay Sullivan, was made. 

Which in all of its name meaning: Poetic Dark-haired Warrior Son of Righteousness.

EDIT: By popular demand on Discord, the fans have made the popular vote for his name in headcanon to be Jackson MacDonald Sullivan.

**Miscellaneous**

He's a year (or month(s) older than June and Quint together, while is a couple years younger than Dirk (who looks and sounds more like 15 years of age in the show to us). 

In our view, Jack has a diverse taste of music based around the mood he's in at the moment; compared to that of Peter Quill.

FACT: Learning the Gaelic languages is actually HARD to learn at beginners' level whereas the other languages (e.g. Spanish, French, and so many other European languages that are hard to list all at once, etc.) are easy to learn from there. The Gaelic languages (including Irish, Scottish, Manx) are ironically difficult to master on the initial stages, but once you get the hang of it, you start to learn more words frequently at intermediate levels before (AND if you're determined and lucky enough) mastering the advanced stages within a year and a half (or so I’ve heard; Kyle said it took him 13 years to understand his native tongue). 

Wolfhard himself is also autistic, which is why we had to add Jack being born with a disorder. 

Jack's ancestry was also inspired by the revelation of Ben Stiller being half-Irish and half-Jewish.


	2. Charles O’Sullivan aka “Angry Grandpa”

**Summary for the Chapter:**

> Jack’s paternal grandfather finally revealed.

** Charles Jonathan Kelly O’Sullivan **

** Birth Name** Charles Jonathan Kelly O’Sullivan

 ** Citizenship** Dual American and Irish citizenry.

 ** Irish** _Séarlas Seanachán Ceallaigh Ó Súilleabháin_

 ** Likes** candy, smoking, drinking, money, revenge, the coast, his friends, and fishing.

**Dislikes** : The nickname "Sully" (short for his surname O’Sullivan), talking about his past (especially about his losses, and the Vietnam War), pranks, people tampering with or eating his food and candy, insults to his pride.

** Family**

  * Martin O’Sullivan (father) †
  * Dustin Chelsea O’Sullivan (née Carlson; mother) †
  * Mae Ruth Jensen (née Belle; ex. O’Sullivan; wife)
  * James Ryan Thomas O’Sullivan (firstborn twin son) †
  * Kieran Macaulay O’Sullivan (second eldest son after James) †
  * Evelyn Saralee O’Sullivan (née Armstrong; daughter-in-law) †
  * Mary Orla Collins (née Maureen Orleigh O’Sullivan; ex MacAulish; daughter)
  * Gregory MacAulish (grandson through Mary and Henry MacAulish)
  * Henry MacAulish (1st son-in-law) †
  * Hugh Collins (2nd son-in-law)
  * Mackenzie Columcille Collins (grandson through Mary and Hughes Collins)
  * Tristan Owen O’Sullivan (grandson through James and Margaret)
  * Jackson Teague Duncan Macaulay O’Sullivan (youngest grandson through Kieran and Evelyn)



** Biography **

** Early Life and Childhood **

Charles was born in Waterville, County Kerry, Ireland to Martin and Dustin (née Carlson) O’Sullivan on October 16, 1935.

The youngest of four children, Charles lived with his older brothers Teague and Duncan, and sister Maureen with his mother Dustin who tried solely raising them on her own after their father left as an act of revenge for (to Charles) an undisclosed reason.  


As a result of the divorce, the family struggled financially which led to them rarely staying at one place too long before moving to the next town over, mostly [Ballinskelligs](https://en.m.wikipedia.org/wiki/Ballinskelligs), Killarney, Tralee, Abbeydorney/[Kilflynn](https://en.m.wikipedia.org/wiki/Kilflynn) and [Listowel](https://en.m.wikipedia.org/wiki/Listowel) before finally settling down permanently in the town of Tralee where he spent the majority of his youth.

Despite being traditionally raised an Irish Catholic while attending Listellick National Primary School (Scoil Lios Teilic), Charles was at odds with the nuns and rebelled against the strictures imposed upon him and was at further odds with his mother at home; who though appeared calm and caring, was a very strict and overbearing disciplinarian that became neglectful, and emotionally (and infrequently, physically) abusive towards her children, especially Charles as he was the youngest.  


Because Irish monolingual speakers were present during that time before the 1980s, Charles’ mother, who only spoke American English, attempted to have Charles learn English and not his father’s native Irish by being homeschooled. However, due to Irish fairytale books being his favorite in reading classes when he finally began attending the local [Gaelscoil](https://en.m.wikipedia.org/wiki/Gaelscoil), Charles disregarded the former and knew only Irish with a smattering of English, forcing his older brothers to be his translator.

* * *

** High school years (1950s)**

In ninth grade, O’Sullivan began attending after-school book club meetings to not only improve his literary skills (as he did poorly in other classes such as math and science) but also avoid persecution as well.

Charles had been constantly bullied for his vertically-challenged lankiness since elementary which led to him feigning illness to stay at home. His older brothers (without his knowledge) enlisted him into a local street boxing joint to “man up” in order to cease the bullying, which did help him become a lot taller and stronger as he got older. It did come to an end eventually however, along with Charles’ popularity in tenth grade when one bully injured his head in an assault, leading to his mother filing a lawsuit against the school which was dismissed because of the school’s immunity to previous lawsuits.  


Encouraged by his older brother Duncan (who was also bullied) and some friends, Charles rounded on his delinquent persecutors by viciously assaulting them during their downtime, leading to one death after overdoing it.

When the authorities arrived, Duncan takes the blame for the death and was arrested, leading to Charles becoming eternally guilt-ridden. This also culminated with his mother’s ambitions increasing to better him into becoming a better man than his own father and brothers, leading him to resent her for the time being.

Despite no longer being a victim of his tormentors who’ve by now moved away to another town over, Charles was ostracized by his school peers in class and the book club due to the incident. For the remainder of his high school years, Charles became insidiously embittered by all of this and as a result, began drinking at age 17 and smoking by age 19.  


* * *

** Graduation and Later Years **

Finally graduating at age 18 in 1953, Charles, still feeling so alienated, began distancing from his family by becoming a compulsive drinker like his father at the local pubs on the outskirts of his hometown and started working with his brother Teague at the docks as a longshoreman. A job that would see him become involved in the family fishing business.

Charles became permanently estranged from his family when his mother discovered the truth about the incident from one of his distant friends. 

Forever disowned from the household; Charles verbally spited his mother with all the hatred he had built up within from the last ten years of his life. This eventually causes her to suffer severe depression that eventually led to her death from a cirrhosis after he refuted her forgiveness years later.

** Arriving in America **

After the drama, one of Charles’ only friends David Jameson, invited him to accompany him on a boat for America because he couldn’t afford a plane ticket to meet his American girlfriend. Using this as means of getting his life back together, Charles agreed and drove his brother’s boat to the nearest state, Massachusetts.

Once he and David arrived at Cape Cod port, Charles life in America began. Though he spoke limited English, David allowed him to stay with him and his girlfriend until he can manage on his own. Helping Charles attend Massachusetts Maritime Academy, his English improved and his first job as a fisherman began paying better in the states, Charles saw a bright future ahead of him.

However, the Vietnam War was still active during all this and being the right age had thus called Charles for [the draft](https://en.m.wikipedia.org/wiki/Conscription_in_the_United_States) when he was 19.

Fortunately, Charles failed the physical examination due to an automobile accident when he was drinking at 17, and thus, avoided service; but his friend David however wasn’t as fortunate. As a result Charles attempted to enlist voluntarily until he was finally admitted to join the infantry that David was in. Unfortunately, David was killed soon after in a bombing raid during one of the failed attacks in northern Vietnam, leaving his pregnant girlfriend and Charles traumatically heartbroken.

The death of his only true friend coupled with already escalating depression left by his sorrows, led to Charles dropping out of college upon his return as poor grades made him ineligible to enroll in an apprenticeship program. Thereafter, Charles stopped speaking for days and didn’t attend David’s funeral after losing contact with his best friend’s girlfriend once she moved away, leaving her and David’s Winnebago to Charles. The young O’Sullivan began his life’s journey focus on his social life for the forthcoming years.

* * *

** Mid-Late 1950s—Early 1960s **

With no friends or family to turn to, and desperate for money, O’Sullivan worked several jobs as a volunteer firefighter, flea market salesman, carpenter, apartment maintenance, and laborer.  


O’Sullivan went through desperate measures to garner more financial gain when he began to struggle; such as selling the Winnebago he had been left with from David’s girlfriend for extra currency, doubling the prices of the original items he bought from dollar stores to sell at the local flea markets, stealing scrap metal or discrete materials around town and cities to pawn; sometimes even digging through garbage to collect plastic bottles and containers to pawn at recycle centers, which all the same, he needed desperately for the money.

His desperation led him to taking serious measures. One notorious example was the day he met his first American friend, Gilbert Hemingway.

Hemingway, who was posing as a wheelchair-bounded Vietnam-veteran on the streets, was selling heroin (wherein the drug effects was unheard of in those days) on the streets the day Charles became involved with him in his drug stint. When Charles bought a pack of cigarettes from him and smoked it at a Jewish Cemetery, he underwent a mescaline which resulted in a vivid hallucination of zombies rising out of the graves, thence creating his fear of the undead. After having a long argument about the drugs, Hemingway offers Charles a job with it, but O’Sullivan refused.

But eventually after getting laid off from one his maintenance jobs, Charles took Hemingway up on his offer and began selling the lesser-known substance at Hemingway’s behest until he was caught by an officer who confiscated it. Charles wasn’t arrested though as its dangerous effects was still unknown. Given only a warning as he was believed to be a con artist, Hemingway, who went through the same thing, was persuaded by Charles to cruise along with him on his brother’s boat to catch fish for a profit, not being bothered by all the life around him. Agreeing to this, Hemingway eventually became Charles’ first mate.

When he wasn’t fishing for his own, Charles and Hemingway found themselves comfortable with the loose routines at the docks as deckhands and longshoremen.

Having made extra that day from his last dead-end maintenance job and plus skilled with the only trait he knew well more than anything, Charles has managed to save enough to buy himself a large fishing yacht (with living quarters) from Provincetown.

Wanting to do some “star traveling during occupation” Charles and Hemingway applied for a job at a Boston local truck station for additional pay to buy alcohol.

While there, they become onetime friends with serial killer [Charles Edward Terry](https://en.m.wikipedia.org/wiki/Charles_E._Terry) in early July during the year 1962 [and had once been involved in a mugging attempt with the latter after Hemingway revealed he owed money to a loan shark; resulting in the three working together to rob a wealthy gay bar owner who did late-evening jogs in the forests near Hemingway’s apartment. However it backfired terribly for the trio as the owner knew martial arts, nearly pulverizing O’Sullivan and Hemingway in the process, and leaving Terry knocked out on the side of the road with their truck and personal possessions stolen during his getaway.](https://m.youtube.com/watch?v=eoZOqyHIECQ)

The incident strained their relationship with Terry, and soon after, lost contact with him. It wasn’t until his arrest in 1963 that Charles found out who he was which sobered him up quickly after the experience. Soon afterwards, he moved and settled in Scituate for a short time before returning to Cape Cod with Hemingway, meeting a new colleague from South Carolina named Angus Thorstein (who Hemingway humorously dubbed “Gus”) along the way en route to the Georgian-Floridian coastline for the seasonal summer catch.

* * *

** Marriage **

In 1964, Charles meets a young Alabaman woman named Mae Ruth Belle from the town of Troy at the coastal town of Mobile, Alabama while on his yearly fishing trip. The two began a friendship that escalated with the time they spend together, eventually culminating in a series of dating and then marriage at the ages of 30, followed by 3 children: twin sons James and Kieran (who were named after Kieran, his fatherly local priest from Ireland, and his best friend David’s surname James) in 1965; and a daughter named after his sister Maureen in 1969.

* * *

** The Troubles (1970s-1980s)**

** (age 30s) **

Initially seeming well off, living either in small-town communities or near the coastline from time-to-time, Charles and his wife made a living off of their combined insurances while also providing their children with their money from their respective careers, Charles, fishery, and Mae, veterinarian and physician.

However, the first time conflict that got between Charles and Mae was when his sister managed to track down and send him a letter to see his dying mother; wanting put aside their differences and forgive one another. But Charles was still bitter about her and burned the letter in the process. Shocked at this, Mae refused to talk to him until he’s explained his actions.

When his mother finally died and the last letter ceased on his birthday, Charles and his wife began to have constant arguments about the matter, straining their marriage furthermore.

Eventually when their sons started to want more independence Charles outright refuses them as a murder had taken place near where they lived (reminiscing him of his close-call with Terry); prompting Charles to become more overly protective which began to take a toll on his family.

When him and his wife no longer see eye-to-eye, Charles began losing it after that. Falling back into drinking once again, he seduced multiple women into bed, which later resulted having at least 7 known children added with his first 3; giving him 10 children in total (though possibly there may be more as there were flings here and there).

Becoming increasingly borderline abusive towards everyone around him, the divorce finally came when his affairs were revealed days after their home got evicted for disturbances and thus, Charles was forced to give up custody of his children.

Depressed, he continuously indulged into more alcohol which did nothing to placate his temper as it became evermore unruly. When a letter from his distant brother Teague requests his return to Ireland about his brother Duncan’s death in prison, Charles moved back to the northern States and left America for the Emerald Isle.

The hostility between Ulster and the Republic of Ireland boiled over into a violent war called the Troubles. At first, Charles wanted no part of it with his brother Teague until he was revealed that Duncan’s death was caused by his old school bullies seeking revenge. Charles took up arms with the volunteers of the IRA after Teague was killed in one of the battles and became heavily immersed in the events that followed from the mid-late seventies (1975–1978).

Charles was among one of those that didn’t have signed documents showing his involvement in the Troubles. However witnesses and former comrades who remember him reaffirm his involvement to authorities later on, forcing him to leave Ireland to escape capture and/or possibly the death penalty.  


* * *

** Return to America**

Upon his return to Massachusetts, Charles is notified by authorities of his children falling victim to an event that was indirectly caused by Mae’s negligence.  


Charles wins custody over his sons James and Kieran in court and (un)justly has a restraining order put out against Mae, leaving himself with joint custody of Maureen with her.  


From then on, Charles forced James and his brother Kieran to begin working at a young age; often enforcing them to play sports at early hours outside instead of playing at the local arcade to get them fit as athletes for manual labor work. Punishing then with physical violence for disobedience and/or discipline.

* * *

** 1980s **

** (age mid 40s) **

As his sons soon reach high school, they become more rebellious and disobedient; avoiding home until late hours in the evening, partying with friends, and steal his car from time to time.

It wasn’t until they both graduate high school that they leave his home without a word, exchanging no letters or knowledge between them. For years to come, Charles wouldn’t hear nor see his sons ever again until that fateful year of 1999.  


* * *

** 1999 **

Charles has since remained alone at home, continuing his job as a fisherman and having successfully recreated his original family fishery business in America with his friends at Boston. However, upon receiving devastating news (via a phone call) that both his sons and daughter-in-law were critically hospitalized; leading him to arrive in time to discover that they have both passed with his daughter-in-law leaving behind a newborn grandson named Jackson by his other grandson (from James) after the family nurse: Loretta Jackson.

Hoping to make things right with his deceased sons, Charles takes in the newborn and older grandson, and tries to raise him, but his jobs however forced him to make arrangements while having his other grandson Tristan (James’ only son) mostly tend to Jackson’s needs, neglecting those responsibilities.

Feeling that Scituate wasn’t meant for his grandsons as it brought back bad memories, Charles chose to return to Ireland once more to make amends with his sister after receiving his inheritance from his deceased siblings and partially his mother.

The next month after, he returned to his hometown of Tralee and settled there for several years.

His time living there had his youngest grandson Jackson growing up knowing the Irish way of life; speaking and writing (only) the Irish Language, attending Mass, and celebrating Irish traditions. Charles’ sister, still angry at him for his behavior towards their mother, was no longer be on speaking terms; resulting in the old man to start drinking again once more, becoming increasingly temperamental and aggressive towards others; mainly his grandsons. As notoriety developed around him, ruminations of his actions during the Troubles began grow, he laid low and utilized different means of earning money. Forcing his grandson Jackson to participate in talent shows to earn more currency, Charles began verbally threatening him into the process of doing so.

Eventually Charles’ feelings of unease have him and his grandsons leave Ireland for good, narrowly avoiding arrest as authorities occupied his former apartment.

* * *

**America (2006—2008)**

Back in Scituate, Charles and his grandsons settled at a mobile home community (which was right next to the sea and beaches). Charles continued drinking and his behavior towards his grandsons grew more volatile overtime as stress became unbearable with his age.

Sending his grandsons to school, his youngest to Inly School (an Montessori school), and his oldest, to Scituate High School, Charles returned to fishing while also making money off his salesmanship at local flea markets and began using his youngest grandson’s [SSI](https://en.wikipedia.org/wiki/Supplemental_Security_Income) benefits after learning Jackson's diagnosis with [ADHD](https://en.wikipedia.org/wiki/Attention_deficit_hyperactivity_disorder) and [Autism](https://en.wikipedia.org/wiki/High-functioning_autism).

Things take a turn for the worst whenever Charles fell in debt with bill collectors due to his drinking and addictions (some of which he shared with Hemingway) and has had health problems involving him becoming overweight from excessive alcoholic drinking and eating of fatty and oily foods such as fish; leading him to undergo [gastric bypass surgery](https://en.m.wikipedia.org/wiki/Gastric_bypass_surgery). However the surgery led to him developing [dumping syndrome](https://en.m.wikipedia.org/wiki/Dumping_syndrome), which became so severe that he became addicted to painkillers.

This attributed to his behavior to becoming volatile around everyone around him as he tried to distance himself personally from others save for Fisheye and Gus. His actions and behavior alone however has gotten him into legal trouble and banned from multiple public areas such as restaurants, and entertainment centers after becoming irked by even the slightest effrontery. One of his drinking sessions landed him in a short-lived coma which got him sent to the urgent care center (where doctors also managed to deduce that he had bipolar disorder).

His behavior constantly warranted attention from child protective services as many of Jackson’s friends at school notified the counselors of neglect and abuse at his hands (most of which turned out to be true though), seeing small scars or bruises on his skin from the leather belt.

Charles ceased most of his habits when one drinking incident traumatizes his grandsons by letting some new neighbors over for a drinking a spar which led to them taking advantage of his stupor. Eventually, he and his grandsons moved away to another residential area in Scituate after an event in City Hall forces him and his grandsons to leave the trailer park they reside in to create a new residence.

After settling into their new home in the woods, Charles tried to make up with his grandsons by taking them fishing on the weekends to make some profit but remained unsuccessful causing his restraint on rage to break as his grandsons’ inabilities waned his patience.

Over the next few years of secretly falling in and out of many states of depression and at one point, attempted suicide; Charles starts falling victim to not just his health and addictions but also these “innocent” pranks off by his grandsons (evoked by his eldest Tristan). Many of these prompts him to become prone to bouts of rage which lead him to destroying multiple household items and appliances while unknowingly being filmed by his youngest Jackson and out on YouTube.

However the pranks end when his eldest creates a false bomb made of defunct road flares and an circular alarm clock to provoke him into frantically diffusing it; but later freaks out and nearly demolished every single object in the living room upon discovering that it was a gag. His relationship with his grandsons is further strained when Federal agents believing it to be a real bomb upon seeing the video online, briefly have him under house arrest while going through his house; and later as neighbors begin to testify against him for abusing his parental rights, have police cruisers surround the neighborhood.

By the time his grandsons were at the ages of 18 and 8, an eviction notice demands he leave the community, he was enraged. Upset that he can no longer be present at the town without being hounded by vigilant neighbors and policemen, Charles decided to permanently resettle at Cape Cod much to his grandsons’ protest.

After verbally taking his anger out on his grandsons, he falls into an argument with Tristan ending with him getting a bloody nose from him and Tristan taking Jackson with him on his motorbike. It took the shamefaced Charles 3 days to track then down after coming to terms with his actions and tried to (in vain) converse with his grandsons at a gas station he found them at.

Angered at this, he chased them down in his truck causing a severe traffic collision to happen on the road, nearly killing his grandsons in the process.

Charles is awakened days later and is cuffed at the hospital and taken to  Massachusetts Correctional Institution  at Concord ( MCI-Concord ) for ten years.

The first 2 years of his imprisonment is unknown due to the unexpected arrival of the Monster Apocalypse. Nothing else is known about him.


End file.
